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  • Phytochemical analysis and in vitro biological activity of three Hypericum species from the Canary Islands (Hypericum reflexum, Hypericum canariense and Hypericum grandifolium).

Phytochemical analysis and in vitro biological activity of three Hypericum species from the Canary Islands (Hypericum reflexum, Hypericum canariense and Hypericum grandifolium).

Fitoterapia (2014-12-03)
Christian Zorzetto, Candelaria C Sánchez-Mateo, Rosa M Rabanal, Giulio Lupidi, Dezemona Petrelli, Luca A Vitali, Massimo Bramucci, Luana Quassinti, Giovanni Caprioli, Fabrizio Papa, Massimo Ricciutelli, Gianni Sagratini, Sauro Vittori, Filippo Maggi
ABSTRACT

In the present work we carried out a phytochemical and biological investigation on three Hypericum species, i.e. Hypericum reflexum, Hypericum canariense and Hypericum grandifolium, from the Canary Islands where they are traditionally used as diuretic, wound healing, vermifuge, sedative and antidepressive agents. The polar extracts of the top flowering aerial parts, prepared by Soxhlet apparatus using a methanol-acetone (1:1) extracting mixture, were analyzed by HPLC-DAD and HPLC-MS for the content of eight biomarkers such as hypericin, hyperforin, chlorogenic acid, rutin, hyperoside, isoquercitrin, quercitrin and quercetin, whereas the hydrodistilled essential oils were analyzed by GC-FID and GC-MS. The three Hypericum species had different results in both polar and volatile constituents, H. reflexum being the only one endowed with a small amount of naphtodianthrones (hypericin and pseudohypericin), and containing high levels of chlorogenic acid, rutin and volatile mono- and sesquiterpenes. After chemical characterization, all products were in vitro biologically assayed for antiproliferative activity on human tumor cell lines by MTT assay, for antioxidant potential by DPPH, ABTS and FRAP assays, and for antimicrobial activity by the agar disc diffusion and microdilution methods. Results revealed interesting bioactivities and differences between polar extracts and essential oils, with the former being endowed with significant antioxidant activity and the latter with comparable inhibition effects on the tumor cells (A375, MDA-MB 231 and HCT 116) to that of cisplatin.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methanol, NMR reference standard
Hyperoside, primary reference standard
Sigma-Aldrich
Quercetin, ≥95% (HPLC), solid
Chlorogenic acid, primary reference standard
Sigma-Aldrich
Quercetin 3-β-D-glucoside, ≥90% (HPLC)
Supelco
(+)-Terpinen-4-ol, analytical standard
Supelco
Heneicosane, analytical standard
Supelco
Eucalyptol, analytical standard
Supelco
p-Cymene, analytical standard
Supelco
Triacontane, analytical standard
Supelco
Palmitic acid, certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland
Sigma-Aldrich
Phosphoric acid solution, NMR reference standard, 85% in D2O (99.9 atom % D), NMR tube size 3 mm × 8 in.
Sigma-Aldrich
Phosphoric acid solution, NMR reference standard, 85% in D2O (99.9 atom % D), NMR tube size 5 mm × 8 in.
Supelco
Palmitic acid, Pharmaceutical Secondary Standard; Certified Reference Material
Millipore
Acetonitrile solution, suitable for HPLC, acetonitrile:water 5:95% (v/v), 10 mM Ammoniumbicarbonate, pH 10,0
Supelco
trans-Nerolidol, analytical standard
Supelco
Undecane, analytical standard
Supelco
(−)-Terpinen-4-ol, analytical standard
Sigma-Aldrich
Palmitic acid, ≥98% palmitic acid basis (GC)
Sigma-Aldrich
Terpinolene, technical, ≥85% (GC)
Supelco
Tridecane, analytical standard
Supelco
Heptadecane, analytical standard
Supelco
Geraniol, analytical standard
Supelco
Tricosane, analytical standard
Supelco
Myrcene, analytical standard
Supelco
Hexacosane, analytical standard
Sigma-Aldrich
Geraniol, ≥97%, FCC, FG
Sigma-Aldrich
p-Cymene, 99%
Sigma-Aldrich
Hexacosane, 99%
Sigma-Aldrich
Dipentene, mixture of isomers